EP1120411B1 - Dérivés de 4-aryl-1,2,4-triazolidinedione et leur utilisation comme herbicides - Google Patents

Dérivés de 4-aryl-1,2,4-triazolidinedione et leur utilisation comme herbicides Download PDF

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Publication number
EP1120411B1
EP1120411B1 EP01110136A EP01110136A EP1120411B1 EP 1120411 B1 EP1120411 B1 EP 1120411B1 EP 01110136 A EP01110136 A EP 01110136A EP 01110136 A EP01110136 A EP 01110136A EP 1120411 B1 EP1120411 B1 EP 1120411B1
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European Patent Office
Prior art keywords
chlorine
diyl
alkyl
fluorine
phenyl
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EP01110136A
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German (de)
English (en)
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EP1120411A2 (fr
EP1120411A3 (fr
Inventor
Karl-Heinz Linker
Kurt Prof. Dr. Findeisen
Otto Dr. Schallner
Andreas Dr. Lender
Hans-Joachim Dr. Santel
Markus Dr. Dollinger
Akihiko Yanagi
Toshio Goto
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Bayer CropScience AG
Bayer CropScience KK
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Bayer CropScience AG
Bayer CropScience KK
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the invention relates to new substituted N-aryl nitrogen heterocycles, processes for their manufacture and their use as herbicides.
  • triazolidine-3,5-dithione derivatives are herbicidal Properties called a mono- or disubstituted phenyl radical can own.
  • N- (trifluoromethanesulfonylaminophenyl) substituted N-heterocycles with herbicidal properties called.
  • Triazolidine-3,5-dione derivatives which, however, have a phenyl radical in comparison to the Compounds according to the invention have different substitution patterns.
  • the compounds of the general formula (I) can also be converted into other compounds of the general formula (I) according to the above definition by further customary methods, for example by customary conversions of carboxylic acid groups or their derivatives (for example R 5 : COOH ⁇ COCl, COOH ⁇ COOCH 3 , COCl ⁇ CONH 2 , COOCH 3 ⁇ CONH 2 , CONH 2 ⁇ CN, CN ⁇ CSNH 2 ), by alkylation reactions (e.g. R 1 : H ⁇ CH 3 or CHF 2 ) or by oxidation or sulfurization (e.g. Q 1 : O ⁇ S or S ⁇ O) - cf. also the manufacturing examples.
  • carboxylic acid groups or their derivatives for example R 5 : COOH ⁇ COCl, COOH ⁇ COOCH 3 , COCl ⁇ CONH 2 , COOCH 3 ⁇ CONH 2 , CONH 2 ⁇ CN, CN ⁇ CSNH 2
  • the new substituted N-aryl nitrogen heterocycles of the general formula (I) are characterized by strong herbicidal activity.
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl each straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.
  • Ar has, for example, the meanings listed below: 2,4,5-trichlorophenyl, 2,4-dichloro-5-fluorophenyl, 2-chloro-4,5-difluorophenyl, 4-chloro-2,5-difluorophenyl, 5-chloro 2,4-difluorophenyl, 2-fluoro-5-chloro-4-cyano-phenyl, 2,4,5-trifluorophenyl, 2,5-dichloro-4-cyano-phenyl, 2-chloro-5- fluoro-4-cyano-phenyl, 2-chloro-4,5-dicyano-phenyl, 2-chloro-4-fluoro-5-cyano-phenyl, 2,5-difluoro-4-cyano-phenyl, 2-chloro 4-cyano-5-methylphenyl, 2,4-dichloro-5-methoxyphenyl, 2,4-dichloro-5-ethoxyphenyl, 2,4-dichlor
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Ar has, for example, the meanings listed above in Group 1.
  • Formula (II) provides a general definition of the (thio) semicarbazide derivatives to be used as starting materials in process (a) according to the invention for the preparation of the compounds of the general formula (I).
  • Q 1 , Q 2 , R 1 , R 2 and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q 1 , Q 2 , R 1 , R 2 and Ar have been given;
  • R preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • aryliso (thio) cyanates of the formula (IV) required as precursors are known and / or can be produced by known processes (cf. DE 4327743, DE 4335438 and DE 4343451).
  • Process (a) according to the invention is preferably carried out in the presence of a suitable one Reaction aid carried out.
  • a suitable one Reaction aid carried out.
  • All the usual inorganic ones come as such or organic bases in question. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as lithium, sodium, potassium or Calcium hydride, lithium, sodium or potassium amide, sodium or potassium methylate, Sodium or potassium ethylate, sodium or potassium propylate, Aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, Ammonium hydroxide, sodium, potassium or calcium acetate, Ammonium acetate, sodium, potassium, rubidium, cesium, magnesium or Calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate, as well as basic organic nitrogen compounds, such as trimethylamine, triethylamine, Tripropylamine, tributy
  • organic solvents come into consideration.
  • these include in particular aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as pentane, hexane, heptane, petroleum ether, ligroin, Petrol, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, Dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, Diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, Ethylene glycol dimethyl or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Ketones such as acetone, butanone
  • reaction temperatures can be carried out when carrying out the process according to the invention
  • Process (a) can be varied over a wide range. Generally works one at temperatures between 0 ° C and + 150 ° C, preferably at temperatures between 10 ° C and 120 ° C.
  • Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible, under increased or reduced pressure - im generally between 0.1 bar and 10 bar - to work.
  • Formula (III) provides a general definition of the aryliminoheterocycles to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I).
  • Q 1 , Q 2 , R 1 , R 2 and Ar preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q 1 , Q 2 , R 1 , R 2 and Ar were given.
  • aryliminoheterocycles of the formula (III) are obtained if aryl (thio) semicarbazide of the general formula (VI) with reactive carbonic acid derivatives, such as e.g. Phosgene or thiophosgene, optionally in the presence of diluents, such as. Toluene and / or dichloromethane, at temperatures between 0 ° C and 100 ° C implements.
  • reactive carbonic acid derivatives such as e.g. Phosgene or thiophosgene
  • Process (b) according to the invention is optionally carried out in the presence of a Reaction aid carried out.
  • a Reaction aid carried out.
  • the same reaction aids come here as in method (a) according to the invention, but also also Alkali metal sulfides, e.g. Sodium or potassium sulfide.
  • Process (b) according to the invention is preferably carried out using a Diluent carried out.
  • the same diluents are used as in process (a) according to the invention.
  • reaction temperatures can be carried out when carrying out the process according to the invention
  • Process (b) can be varied over a wide range. Generally works one at temperatures between 0 ° C and + 250 ° C, preferably at temperatures between 20 ° C and 150 ° C.
  • Process (b) according to the invention is generally carried out under normal pressure. However, it is also possible, under increased or reduced pressure - im generally between 0.1 bar and 10 bar - to work.
  • the active compounds according to the invention can be used as defoliants, desiccants, and herbicides and especially used as a weed killer. Weeds in the broadest sense are all plants that grow in places, where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount applied.
  • the active compounds according to the invention can e.g. in the following plants be used:
  • the compounds are suitable for combating total weeds e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the weed control compounds in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, Banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control be used in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for selective control of monocot and dicot weeds in monocotyledons Cultures both pre-emergence and post-emergence.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic Solvents are used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as Chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • solid carriers e.g. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granulates are possible: e.g.
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • dispersants for example lignin sulfite waste liquor and methyl cellulose.
  • adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids.
  • Further Additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.
  • Known herbicides for example anilides, are suitable for the mixtures.
  • Aryl carboxylic acids e.g. Dichlorpicolin acid, Dicamba and picloram
  • Aryloxyalkanoic acids e.g. 2,4-D, 2,4-DB, 2,4-DP, Fluroxypyr, MCPA, MCPP and triclopyr
  • Aryloxy-phenoxy-alkanoic acid esters such as e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and Quizalofop-ethyl
  • Azinones e.g.
  • Chloridazon and norflurazon Carbamates like e.g. Chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, such as. Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, bifenox, fluoroglycofen, fomesafen, Halosafen, lactofen and oxyfluorfen; Ureas, e.g.
  • Amidosulfuron bensulfuron-methyl, chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Metsulfuron-methyl, Nicosulfuron, Primisulfuron, Pyrazosulfuron-ethyl, Thifensulfuron-methyl, Triasulfuron and Tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialates, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallate; Triazines, e.g.
  • Atrazin cyanazin, simazin, simetryne, terbutryne and terbutylazin; triazinones such as. Hexazinone, metamitron and metribuzin; Others, such as aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • triazinones such as. Hexazinone, metamitron and metribuzin
  • Others such as aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyph
  • a mixture with other known active ingredients such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.
  • the active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. They are used in the usual way, e.g. by pouring, spraying, Spray, sprinkle.
  • the active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be worked into the soil before sowing become.
  • the amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Example 3 The compound listed in Table 1 as Example 3 can be produced, for example, as follows:
  • Example 9 The compound listed in Table 1 as Example 9 can be produced, for example, as follows:
  • Example 24 the compound listed in Table 1 as Example 24 can be made as follows:
  • Example 25 The compound listed in Table 1 as Example 25 can be produced, for example, as follows:
  • Example 26 The compound listed in Table 1 as Example 26 can be produced, for example, as follows:
  • Seeds of the test plants are sown in normal soil and watered with the preparation of active compound after 24 hours.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
  • the compounds according to the preparation examples show 1, 2, 3, 4 and 5 with good application rates of 60 g / ha to crops, e.g. Barley and corn (10-70%) and very strong Action against weeds such as Alopecurus (90-100%), Cynodon (95 -100%), Setaria (70-100%), Amaranthus (90-100%), Chenopodium (100%), Matricaria (95-100%), Polygonum (80-100%), Portulaca (95-100%) and Viola (90-100%).
  • the active ingredient preparation is used to inject test plants which have a height of 5 - 15 cm have so that the desired amounts of active ingredient per unit area be applied. After three weeks, the degree of damage to the plants rated in% damage compared to the development of the untreated Control.
  • the compounds according to the preparation examples show 1, 2, 3, 4 and 5 with application rates between 15 and 250 g / ha strong Action against weeds such as amaranthus (60-100%), chenopodium (90-100%), Datura (80-100%), Galium (90-100%) and Veronica (50-100%).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (7)

  1. N-Arylhétérocycles azotés substitués de la formule générale (I) :
    Figure 00730001
       dans laquelle :
    Q1 représente l'atome d'oxygène ou de soufre,
    Q2 représente l'atome d'oxygène ou de soufre,
    R1 représente un radical alcoyle en C1-C6 le cas échéant substitué par l'atome de fluor ou de chlore,
    R2 représente un radical alcoyle en C1-C6 le cas échéant substitué par l'atome de fluor ou de chlore,
    Ar représente le groupement aryle monocyclique, substitué, défini ci-après :
    Figure 00730002
       où
       R3 représente l'atome de fluor, de chlore ou de brome,
       R4 représente l'atome d'hydrogène, de fluor, de chlore ou de brome,
       R5 représente le radical cyano, carboxy, chlorocarbonyle, carbamoyle, thiocarbamoyle, hydroxy, l'atome de fluor, de chlore, de brome, ou représente un radical alcoyle, alcoxy ou alcoxycarbonyle, avec chaque fois, jusqu'à 4 atomes de carbone, chaque fois le cas échéant substitué par l'atome de fluor et/ou de chlore,
       R6 représente le groupement suivant : -A1-A2-A3    dans lequel :
    A1 représente une simple liaison ou l'atome d'oxygène, de soufre, le radical -SO-, -SO2-, -CO- ou le groupement -N-A4-, où A4 représente l'atome d'hydrogène, le radical hydroxy, un radical alcoyle en C1-C4, alcényle en C3-C4, alcynyle en C3-C4, alcoxy en C1-C4, phényle, (alcoyl en C1-C4)carbonyle, phénylcarbonyle, (alcoyl en C1-C4)sulfonyle, phénylsulfonyle,
    A1 représente par ailleurs, un radical alcanediyle en C1-C6, alcènediyle en C2-C6, azaalcènediyle en C2-C6, alcynediyle en C2-C6, cycloalcanediyle en C3-C6, cycloalcènediyle en C3-C6 ou phénylène, chaque fois le cas échéant substitué par l'atome de fluor, de chlore ou de brome,
    A2 représente une simple liaison ou l'atome d'oxygène, de soufre, le radical -SO-, -SO2-, -CO- ou le groupement -N-A4-, où A4 représente l'atome d'hydrogène, le radical hydroxy, un radical alcoyle en C1-C4, alcoxy en C1-C4, phényle, (alcoyl en C1-C4)sulfonyle ou phénylsulfonyle,
    A2 représente par ailleurs, un radical alcanediyle en C1-C6, alcènediyle en C2-C6, azaalcènediyle en C2-C6, alcynediyle en C2-C6, cycloalcanediyle en C3-C6, cycloalcènediyle en C3-C6 ou phénylène, chaque fois le cas échéant substitué par l'atome de fluor, de chlore ou de brome,
    A3 représente l'atome d'hydrogène, avec la condition que dans ce cas, A1 et/ou A2 ne représentent pas une simple liaison,
    A3 représente par ailleurs, le radical hydroxy, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyle, thiocarbamoyle, sulfo, chlorosulfonyle, l'atome de fluor, de chlore, de brome,
    A3 représente par ailleurs, un radical alcoyle, alcoxy, alcoylthio, alcoylsulfinyle, alcoylsulfonyle, alcoylamino, dialcoylamino, alcoxycarbonyle ou dialcoxy(thio)phosphoryle avec chaque fois, 1 à 6 atomes de carbone dans les radicaux alcoyle, chaque fois le cas échéant substitué par l'atome de fluor, de chlore ou le radical alcoxy en C1-C4,
    A3 représente par ailleurs, un radical alcényle, alcényloxy, alcénylamino, alcoylidèneamino, alcényloxycarbonyle, alcynyle, alcynyloxy, alcynylamino ou alcynyloxycarbonyle avec chaque fois, 2 à 6 atomes de carbone dans les radicaux alcényle, alcoylidène ou alcynyle, chaque fois le cas échéant substitué par l'atome de fluor ou de chlore,
    A3 représente par ailleurs, un radical cycloalcoyle, cycloalcoxy, cycloalcoylalcoyle, cycloalcoylalcoxy, cycloalcoylidèneamino, cycloalcoyloxycarbonyle ou cycloalcoylalcoxycarbonyle, avec chaque fois, 3 à 6 atomes de carbone dans les radicaux cycloalcoyle, et le cas échéant, 1 à 4 atomes de carbone dans les radicaux alcoyle, chaque fois le cas échéant substitué par l'atome de fluor, de chlore, le radical cyano, carboxy, un radical alcoyle en C1-C4 ou (alcoxy en C1-C4)carbonyle,
    A3 représente par ailleurs, un radical phényle, phényloxy, phényl(alcoyle en C1-C4), phényl(alcoxy en C1-C4), phényloxycarbonyle ou phényl(alcoxy en C1-C4)carbonyle, chaque fois le cas échéant substitué par le radical nitro, cyano, carboxy, l'atome de fluor, de chlore, de brome, un radical alcoyle en C1-C4, halogénoalcoyle en C1-C4 et/ou (alcoxy en C1-C4)carbonyle,
    A3 représente par ailleurs, un radical pyrrolyle, pyrazolyle, imidazolyle, triazolyle, furyle, oxirannyle, oxétannyle, dioxolannyle, thiényle, oxazolyle, isoxazolyle, thiazolyle, isothiazolyle, oxadiazoylyle, thiadiazolyle, pyridinyle, pyrimidinyle, triazinyle, pyrazolyl (alcoyle en C1-C4), furyl(alcoyle en C1-C4), thiényl(alcoyle en C1-C4), oxazolyl(alcoyle en C1-C4), isoxazolyl (alcoyle en C1-C4), thiazolyl(alcoyle en C1-C4), pyridinyl(alcoyle en C1-C4), pyrimidinyl(alcoyle en C1-C4), pyrazolylméthoxy, furylméthoxy, chaque fois le cas échéant complètement ou partiellement hydrogéné, représente le radical perhydropyrannylméthoxy ou pyridylméthoxy, et
    R7 représente l'atome d'hydrogène, de fluor ou de chlore.
  2. Composés selon la revendication 1, caractérisés en ce que
       Q1 représente l'atome d'oxygène ou de soufre,
       Q2 représente l'atome d'oxygène ou de soufre,
       R1 représente le radical méthyle, éthyle, n- ou i-propyle, n-, i-, s- ou t-butyle, le cas échéant substitué par l'atome de fluor ou de chlore,
       R2 représente le radical méthyle, éthyle, n- ou i-propyle, n-, i-, s- ou t-butyle, le cas échéant substitué par l'atome de fluor ou de chlore,
       Ar représente le groupement aryle monocyclique, substitué, défini ci-après :
    Figure 00770001
       où
       R3 représente l'atome de fluor ou de chlore,
       R4 représente l'atome d'hydrogène, de fluor ou de chlore,
       R5 représente le radical cyano, thiocarbamoyle, l'atome de chlore, de brome, le radical trifluorométhyle, méthoxy, difluorométhoxy ou trifluorométhoxy,
       R6 représente le groupement suivant : -A1-A2-A3    dans lequel :
    A1 représente une simple liaison ou l'atome d'oxygène, de soufre, le radical -SO-, -SO2-, -CO- ou le groupement -N-A4-, où A4 représente l'atome d'hydrogène, le radical hydroxy, méthyle, éthyle, n- ou i-propyle, méthoxy, éthoxy, n- ou i-propoxy, méthylsulfonyle ou éthylsulfonyle,
    A1 représente par ailleurs, le radical méthylène, éthane-1,1-diyle, éthane-1,2-diyle, propane-1,1-diyle, propane-1,2-diyle, propane-1,3-diyle, éthène-1,2-diyle, propène-1,2-diyle, propène-1,3-diyle, éthyne-1,2-diyle, propyne-1,2-diyle ou propyne-1,3-diyle,
    A2 représente une simple liaison ou l'atome d'oxygène, de soufre, le radical -SO-, -SO2-, -CO- ou le groupement -N-A4-, où A4 représente l'atome d'hydrogène, le radical hydroxy, méthyle, éthyle, n- ou i-propyle, méthoxy, éthoxy, n- ou i-propoxy, méthylsulfonyle, éthylsulfonyle, n- ou i-propylsulfonyle ou phénylsulfonyle,
    A2 représente par ailleurs, le radical méthylène, éthane-1,1-diyle, éthane-1,2-diyle, propane-1,1-diyle, propane-1,2-diyle, propane-1,3-diyle, éthène-1,2-diyle, propène-1,2-diyle, propène-1,3-diyle, éhyne-1,2-diyle, propyne-1,2-diyle ou propyne-1,3-diyle,
    A3 représente l'atome d'hydrogène, avec la condition que dans ce cas, A1 et/ou A2 ne représentent pas une simple liaison,
    A3 représente par ailleurs, le radical hydroxy, amino, cyano, nitro, carboxy, carbamoyle, sulfo, l'atome de fluor, de chlore, de brome,
    A3 représente par ailleurs, le radical méthyle, éthyle, n- ou i-propyle, n-, i-, s- ou t-butyle, n-, i-, s- ou t-pentyle, méthoxy, éthoxy, n- ou i-propoxy, n-, i-, s- ou t-butoxy, n-, i-, s- ou t-pentoxy, méthylthio, éthylthio, n- ou i-propylthio, n-, i-, s- ou t-butylthio, méthylsulfonyle, éthylsulfonyle, n- ou i-propylsulfonyle, méthylamino, éthylamino, n- ou i-propylamino, n-, i-, s- ou t-butylamino, diméthylamino, diéthylamino, méthoxycarbonyle, éthoxycarbonyle, n- ou i-propoxycarbonyle, diméthoxyphosphoryle, diéthoxyphosphoryle ou dipropoxyphosphoryle, diisopropoxyphosphoryle, chaque fois le cas échéant substitué par l'atome de fluor, de chlore ou le radical méthoxy ou éthoxy,
    A3 représente par ailleurs, le radical propényle, butényle, propényloxy, butényloxy, propénylamino, buténylamino, propylidèneamino, butylidèneamino, propényloxycarbonyle, butényloxycarbonyle, propynyle, butynyle, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyle ou butynyloxycarbonyle, chaque fois le cas échéant substitué par l'atome de fluor ou de chlore,
    A3 représente par ailleurs, le radical cyclopropyle, cyclobutyle, cyclopentyle, cyclohexyle, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylméthyle, cyclobutylméthyle, cyclopentylméthyle, cyclohexylméthyle, cyclopropylméthoxy, cyclobutylméthoxy, cyclopentylméthoxy, cyclohexylméthoxy, cyclopentylidèneamino, cyclohexylidèneamino, cyclopentyloxycarbonyle, cyclohexyloxycarbonyle, cyclopentylméthoxycarbonyle ou cyclohexylméthoxycarbonyle, chaque fois le cas échéant substitué par l'atome de fluor, de chlore, le radical cyano, carboxy, méthyle, éthyle, n- ou i-propyle, méthoxycarbonyle ou éthoxycarbonyle,
    A3 représente par ailleurs, le radical phényle, phényloxy, benzyle, phényléthyle, benzyloxy, phényloxycarbonyle, benzyloxycarbonyle, chaque fois le cas échéant substitué par le radical nitro, cyano, carboxy, l'atome de fluor, de chlore, de brome, le radical méthyle, éthyle, n- ou i-propyle, trifluorométhyle, méthoxy, éthoxy, n- ou i-propoxy, difluorométhoxy, trifluorométhoxy, méthoxycarbonyle et/ou éthoxycarbonyle,
    A3 représente par ailleurs, un radical pyrrolyle, pyrazolyle, imidazolyle, triazolyle, furyle, thiényle, oxazolyle, isoxazolyle, thiazolyle, isothiazolyle, oxadiazoylyle, thiadiazolyle, pyridinyle, pyrimidinyle, triazinyle, pyrazolylméthyle, furylméthyle, thiénylméthyle, oxazolylméthyle, isoxazolylméthyle, thiazolylméthyle, pyridinylméthyle, pyrimidinylméthylé, pyrazolylméthoxy, furylméthoxy ou pyridylméthoxy, chaque fois le cas échéant complètement ou partiellement hydrogéné,
    R7 représente l'atome d'hydrogène, de fluor ou de chlore.
  3. Procédé de préparation de composés suivant la revendication 1 ou 2, caractérisé en ce que
    (a) on condense par cyclisation, des dérivé (thio)semicarbazide de la formule générale (II) :
    Figure 00810001
       dans laquelle :
    Q1, Q2, R1, R2 et Ar ont les significations données à la revendication 1, et
    R représente un radical alcoyle,
    le cas échéant en présence d'un auxiliaire de réaction et le cas échéant en présence d'un agent de dilution, et le cas échéant à la suite de cela, dans le cadre de la définition des substituants, on réalise des réactions de substitution électrophile ou nucléophile de manière usuelle,
       ou en ce que
    (b) on isomérise de manière thermique (« pyrolytique ») des aryliminohétérocycles de la formule générale (III) :
    Figure 00810002
       dans laquelle :
    Q1, Q2, R1, R2 et Ar ont les significations données ci-dessus,
    le cas échéant en présence d'un auxiliaire de réaction et le cas échéant, en présence d'un agent de dilution.
  4. Agent herbicide, caractérisé par une teneur en au moins un composé selon la revendication 1 ou 2.
  5. Procédé pour lutter contre les plantes non souhaitées, caractérisé en ce que l'on fait agir un composé selon la revendication 1 ou 2 sur les plantes non souhaitées et/ou sur leur biotope.
  6. Utilisation d'un composé selon la revendication 1 ou 2, pour lutter contre les plantes non souhaitées.
  7. Procédé de préparation d'agents herbicides, caractérisé en ce que l'on mélange un composé selon la revendication 1 ou 2 avec des agents de dilution et/ou des substances tensioactives.
EP01110136A 1994-12-15 1995-12-04 Dérivés de 4-aryl-1,2,4-triazolidinedione et leur utilisation comme herbicides Expired - Lifetime EP1120411B1 (fr)

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DE4444741 1994-12-15
DE4444741 1994-12-15
DE19531152 1995-08-24
DE19531152A DE19531152A1 (de) 1994-12-15 1995-08-24 Substituierte N-Aryl-Stickstoffheterocyclen
EP95942066A EP0797573B1 (fr) 1994-12-15 1995-12-04 Derives de 4-heteroaryles-1,2,4-triazole presentant des proprietes herbicides

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DE19627901A1 (de) * 1996-07-11 1998-01-15 Bayer Ag Substituierte aromatische Carbonylverbindungen und ihre Derivate
DE19708928A1 (de) * 1997-03-05 1998-09-10 Bayer Ag Substituierte aromatische Aminoverbindungen
DE19937772A1 (de) 1999-08-10 2001-02-15 Bayer Ag Substituierte Heterocyclyl-2GH-chromene
US7741485B2 (en) * 2003-04-08 2010-06-22 Basf Aktiengesellschaft Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds
US7972867B2 (en) 2005-04-06 2011-07-05 Quest Diagnostics Investments Incorporated Methods for detecting vitamin D metabolites by mass spectrometry
US7745226B2 (en) 2005-04-06 2010-06-29 Quest Diagnostics Investments Incorporated Methods for detecting vitamin D metabolites
US7972868B2 (en) 2007-11-28 2011-07-05 Quest Diagnostics Investments Incorporated Methods for detecting dihydroxyvitamin D metabolites by mass spectrometry
UA105182C2 (ru) * 2008-07-03 2014-04-25 Ньюрексон, Інк. Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность
US7977117B2 (en) 2009-12-03 2011-07-12 Quest Diagnostics Investments Incorprated Vitamin D metabolite determination utilizing mass spectrometry following derivatization
US8034627B2 (en) 2009-12-03 2011-10-11 Quest Diagnostics Investments Incorporated Methods for detecting dihydroxyvitamin D metabolites by mass spectrometry
CN102812356B (zh) 2009-12-11 2017-08-08 奎斯特诊断投资公司 多重样品中的甾族化合物的质谱法
CA2783797C (fr) 2009-12-11 2021-06-08 Quest Diagnostics Investments Incorporated Determination par spectrometrie de masse de vitamine d non metabolisee, non derivee
CN103221409B (zh) 2010-10-01 2016-03-09 巴斯夫欧洲公司 除草的苯并*嗪酮类
PL2688885T3 (pl) * 2011-03-22 2016-12-30 Amidy kwasu N-(1,3,4-oksdiazol-2-ilo)arylokarboksylowego i ich zastosowanie jako herbicydów
CN104072430B (zh) * 2014-07-23 2017-09-29 西华师范大学 多取代的1，2，4‑三唑烷衍生物制备方法
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CN111356693A (zh) 2017-11-23 2020-06-30 巴斯夫欧洲公司 除草的苯基醚类

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JP2007131646A (ja) 2007-05-31
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DE19531152A1 (de) 1996-06-20
HK1008992A1 (en) 1999-07-23
EP0797573B1 (fr) 2002-04-10
US6162765A (en) 2000-12-19
JP4157161B2 (ja) 2008-09-24
ES2174973T3 (es) 2002-11-16
CA2207628C (fr) 2007-01-30
DE59510947D1 (de) 2004-10-28
EP0797573A1 (fr) 1997-10-01
DE59510161D1 (de) 2002-05-16
JPH10510283A (ja) 1998-10-06
US20030144522A1 (en) 2003-07-31
ES2228691T3 (es) 2005-04-16
CN1325848A (zh) 2001-12-12
CN1171879C (zh) 2004-10-20
CA2207628A1 (fr) 1996-06-20
EP1120411A2 (fr) 2001-08-01
CN1090623C (zh) 2002-09-11
US20030208073A1 (en) 2003-11-06
US6743755B2 (en) 2004-06-01
EP1120411A3 (fr) 2001-08-08
CN1175249A (zh) 1998-03-04
AU4340296A (en) 1996-07-03
US6426318B1 (en) 2002-07-30

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